Cyclobutadiene 环丁二烯
Cyclobutadiene is the smallest [n]-annulene ([4]-annulene), an extremely unstable hydrocarbon having a lifetime shorter than five seconds in the free state. It has chemical formula C4H4. It is believed to be in equilibrium between a pair of rectangular/nonplanar ground states and a square, excited triplet state based upon theoretical calculations, and through spectroscopic and crystallographic investigation of substituted cyclobutadienes, in an argon matrix and inside ****. Though it has alternating single and double bonds, it is predicted triplet, unstable and antiaromatic by Hückel's rule, because its ring has 4 π-electrons, and 4 is not twice an odd number. Some cyclobutadiene–metal compounds are stable, thought to be caused by the metal atom providing 2 more electrons to the system. Planar, rectangular distortion to a singlet ground state is caused by the Jahn–Teller effect. Tetra-t-butyl substituted cyclobutadiene is sufficiently stable to gather x-ray crystallographic images of the structure which has a distorted, nonplanar configuration and double bond lengths longer than normal (1.464 vs expected 1.34)